Proton affinityThe proton affinity (PA, Epa) of an anion or of a neutral atom or molecule is the negative of the enthalpy change in the reaction between the chemical species concerned and a proton in the gas phase: A−+H+⟶HA{\displaystyle {\ce {A- + H+ -> HA}}}B+H+⟶BH+{\displaystyle {\ce {B + H+ -> BH+}}}These reactions are always exothermic in the gas phase, i.e. energy is released (enthalpy is negative) when the reaction advances in the direction shown above, while the proton affinity is positive.
Organometallic chemistryOrganometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbonatom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and sometimes broadened to include metalloids like boron, silicon, and selenium, as well.
Organic chemistryOrganic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials (i.e. matter in its various forms that contain carbonatoms). It involves studying the structure of organic material to determine the structural formula, analyzing physical and chemical properties, and evaluating chemical reactivity to understand the behavior of organic compounds.
Lithium diisopropylamideLithium diisopropylamide (commonly abbreviated LDA) is a chemical compound with the molecular formula LiN(CH(CH3)2)2. It is used as a strong base and has been widely utilized due to its good solubility in non-polar organic solvents and non-nucleophilic nature. It is a colorless solid, but is usually generated and observed only in solution.
Base (chemistry)In chemistry, there are three definitions in common use of the word "base": Arrhenius bases, Brønsted bases, and Lewis bases. All definitions agree that bases are substances that react with acids, as originally proposed by G.-F. Rouelle in the mid-18th century. In 1884, Svante Arrhenius proposed that a base is a substance which dissociates in aqueous solution to form hydroxide ions OH.
AmidineAmidines are organic compounds with the functional group RC(NR)NR2, where the R groups can be the same or different. They are the imine derivatives of amides (RC(O)NR2). The simplest amidine is formamidine, HC(=NH)NH2. Examples of amidines include: DBUdiminazenebenzamidinePentamidineParanylinePreparationA common route to primary amidines is the Pinner reaction. Reaction of the nitrile with alcohol in the presence of acid gives an iminoether.
PhosphazenePhosphazenes refer to various classes of organophosphorus compounds featuring phosphorus(V) with a double bond between P and N. One class of phosphazenes have the formula R−N=P(−NR2)3. These phosphazenes are also known as iminophosphoranes and phosphine imides. They are superbases.
AlkoxideIn chemistry, an alkoxide is the conjugate base of an alcohol and therefore consists of an organic group bonded to a negatively charged oxygen atom. They are written as RO, where R is the organylsubstituent. Alkoxides are strong bases and, when R is not bulky, good nucleophiles and good ligands. Alkoxides, although generally not stable in protic solvents such as water, occur widely as intermediates in various reactions, including the Williamson ether synthesis.
GuanidineNames Preferred IUPAC nameGuanidineOther names AminomethanamidineIminomethanediamineCarbamimidamideIdentifiers CAS Number113-00-83D model (JSmol)Interactive imageBeilstein Reference506044 ChEBICHEBI:42820ChEMBLChEMBL821ChemSpider3400DrugBankDB00536ECHA InfoCard100.003.656EC Number204-021-8Gmelin Reference100679 IUPHAR/BPS4783MeSHGuanidinePubChemCID3520UNIIJU58VJ6Y3BCompTox Dashboard(EPA)DTXSID0023117InChIInChI=1S/CH5N3/c2-1(3)4/h(H5,2,3,4)Key: ZRALSGWEFCBTJO-UHFFFAOYSA-NSMILESNC(N)=NProperties Chemical formulaCH5N3Molar mass59.072 g·mol Melting point50 °C (122 °F; 323 K) Solubility in water18.4 mg/100 mLlog P−1.251 Vapor pressure4.1 mmHg (0.55 kPa) Acidity (pKa) 13.6 Basicity (pKb) 0.4 Conjugate acidGuanidinium Thermochemistry Std enthalpy offormation(ΔfH298)−56±1 kJ⋅molStd enthalpy ofcombustion(ΔcH298)−1052.1±1 kJ⋅molPharmacology Pharmacokinetics: Biological half-life7–8 hours Hazards GHS labelling: PictogramsSignal wordWarningHazard statementsH302, H315, H319, H332Related compounds Related compoundsUreaBiguanideExcept where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).Yverify ( ?)
International Union of Pure and Applied ChemistryThe International Union of Pure and Applied Chemistry (IUPAC) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is a member of the International Science Council (ISC). IUPAC is registered in Zürich, Switzerland, and its administrative office, known as the "IUPAC Secretariat", is in Research Triangle Park, North Carolina, United States.Organic synthesisOrganic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the general subject of organic synthesis, there are many different types of synthetic routes that can be completed including total synthesis, stereoselective synthesis, automated synthesis, and many more.
Chemical compoundA chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element is therefore not a compound. A compound can be transformed into a different substance by a chemical reaction, which may involve interactions with other substances.
1,8-Bis(dimethylamino)naphthalene1,8-Bis(dimethylamino)naphthalene is an organic compound with the formula C10H6(NMe2)2 (Me = methyl). It is classified as a peri-naphthalene, i.e. a 1,8-disubstituted derivative of naphthalene. Owing to its unusual structure, it exhibits exceptional basicity. It is often referred by the trade name Proton Sponge, a trademark of Sigma-Aldrich.*As an Amazon Associate I earn from qualifying purchases.